This Week In Startups

A few weeks ago Jason Calacanis stopped by our new offices and recorded an episode of This Week In Startups. It was a fun chat, almost an hour long. My audio is not as good as the audio on Jason so it's a bit hard to hear me unless you want to hear Jason shouting.

If you want to fast forward through the sponsorship message, go to 6:30 and start there.

If you want to fast forward through parts of the discussion, here is the breakdown:

0:00-1:00 Welcome to TWiST from NYC in the Union Square Ventures' offices.1:00-2:00 Thank you to iStockphoto for sponsoring the show.2:00-6:30 Demonstration of how easy it is to purchase high-quality photos within iStockphoto.6:30-8:00 Welcome to Fred Wilson, principal at Union Square Ventures.8:00-8:30 Jason: The biggest mistake of my career was not listening to [Fred’s] wife when she advised me to go national with Silicon Alley Reporter.8:30-9:30 How much of being a VC is being a therapist to the entrepreneurs?9:30-10:30 You’ve worked with Mark Pincus, what was that like?10:30-11:45 You invested in all four of Mark’s companies, yes?11:45-14:00 When Mark came to you for the fourth time with Zynga, what did you say?14:00-15:15 The same sort of situation happened with Twitter, didn’t it?15:15-16:30 If a VC flies out to see you–the entrepreneur–you know there’s serious intent.17:45-19:15 So speed is the big difference between web 1.0 and now?19:15-20:15 Have you ever spoken for your companies too much on your blog?20:15-20:45 Your blog has really made you into one of the most well-known east coast VCs around today.20:45-22:30 How much of your success this time around has been because of the blog?22:30-23:30 Did you enable too much transparency and lose some of your power?23:30-24:30 If money’s not an issue, why go to a VC?24:30-25:00 Are there funds that are now following Union Square Ventures?25:00-26:00 Thank you to MailChimp for sponsoring the show.26:00-29:30 Demonstration of how you can segment your lists to target your emails using MailChimp.29:30-30:00 Fred explains why he would like to see entrepreneurs work backwards and think about who they would like to invest in them.30:00-32:15 How do you reconcile this, the new golden era of Internet companies, with the scars you have from past fund failures?32:15-33:00 When do founders start thinking, “I should start a new company?”33:00-35:15 Let’s talk about entrepreneurs. What are you looking to see in the eyes of an entrepreneur?35:15-37:00 So you’re looking for a persuasiveness that is so strong, people can’t help but follow that person?37:00-38:15 Do you find that this new generation of founders has an entitlement issue, thinking that they’re owed success?38:15-39:15 Does that make that person impossible to manage?39:15-42:15 Are you on the secondary markets? What’s your take on that?42:15-43:45 Fred: Are Mahalo shares being traded?43:45-45:30 Are limited partners stoked about the secondary market?45:30-46:15 Why does a venture firm put money into a single established company and not into several startups?46:15-48:30 What does an opportunity fund mean?48:30-49:00 Fred: In the private equity business, you buy one and you’re done. In the venture business, you make multiple investments and the risks are mitigated.49:00-50:40 What’s your advice for a young entrepreneur who wants your money?50:40-51:15 Fred, it’s been great to watch you rise over the years. Thank you so much.51:15-51:45 Thank you again to our sponsors. We appreciate all of your support!